There is an ongoing need in the fragrance industry to provide chemicals with strong odors so that less fragrance is needed to accomplish the desired odor effect. This, therefore, gives perfumers and other persons the freedom to create new fragrances for perfumes, colognes and personal care products without the limitation of cost. In addition to odor strength, practical considerations such as the scale of synthesis operation may also determine the applicability of identified fragrance molecules in commercial use. However, whether the production of a given fragrance molecule can be carried out at a commercial scale is sometimes unpredictable. For these reasons, continuous effort has been made in fragrance industry to investigate and develop economical processes for making fragrance molecules that possess high strength.
One skilled person recognizes and appreciates the combinations of existing fragrance ingredients that possess superior effect when compared to individual ingredients. Such combinations are considered unexpected and inventive (See, for example, U.S. Pat. No. 7,767,640 and U.S. Pat. No. 7,846,886).
Dec-6-enal is identified as a flavorant in dry parsley (See, Masanetz et al.). Dec-7-enal is employed to reduce the alcohol odor and alcohol sting, but it acts differently from a traditional perfume, wherein a traditional perfume overpowers the alcohol odor or sting by making compositions smell like the perfume (See, U.S. Pat. No. 5,843,881). Dec-8-enal falls under a generic structure that is disclosed as having potential fragrance use (See, U.S. Publication No. 2011/0142776). However, the generic structure as taught covers a wide range of compounds and the synthetic method as described cannot lead to the synthesis of dec-8-enal.
Thus, dec-6-enal, dec-7-enal, and dec-8-enal were each individually reported since early 1990's with various flavor and fragrance properties. They were extracted from natural resources or synthesized via methods that required multi-steps and suffered from long reaction times leading to complex and expensive procedures. To date, none of dec-6-enal, dec-7-enal, and dec-8-enal has achieved commercial importance as a fragrance material. More importantly, nothing set forth in the prior art discloses a mixture of dec-6-enal, dec-7-enal, and dec-8-enal having specified ratios.
The present invention has discovered a convenient and economical process that provides a novel mixture of dec-6-enal, dec-7-enal, and dec-8-enal. The present invention has further surprisingly and unexpectedly discovered that this novel decenal mixture, only when in specified mixing ratios, possesses desirable fragrance properties of high strength that are suitable for fragrance application.